Hadacidin
Structural Formula Vector Image
Title: Hadacidin
CAS Registry Number: 689-13-4
CAS Name: N-Formyl-N-hydroxyglycine
Additional Names: N-formyl-N-hydroxyaminoacetic acid; N-hydroxyformamidoacetic acid
Molecular Formula: C3H5NO4
Molecular Weight: 119.08
Percent Composition: C 30.26%, H 4.23%, N 11.76%, O 53.74%
Literature References: Antitumor antibiotic originally isolated from cultures of Penicillium frequentans Westling. Synthesis: Kaczka et al., Biochemistry 1, 340 (1962); Kinnel, Schoenewaldt, US 3154578 (1964 to Merck & Co.). Biosynthesis: Stevens, Emery, Biochemistry 5, 74 (1966). Review: Shigeura, "Hadacidin" in Antibiotics I, D. Gottlieb, P. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 451-456.
Properties: Unstable crystals, mp 119-120°. Turns brown and liquefies on standing. The decompn products are formic acid and N-hydroxyglycine. Dibasic acid, potentiometric titration shows pH peak at 3.5 and 9.1. Soluble in water, methanol, ethanol, acetone, ether.
Melting point: mp 119-120°
 
Derivative Type: Monosodium salt
Molecular Formula: C3H4NNaO4
Molecular Weight: 141.06
Percent Composition: C 25.54%, H 2.86%, N 9.93%, Na 16.30%, O 45.37%
Properties: Crystals. Easily forms a hydrate, very freely sol in water.

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